Discover the Best Places to Visit in Tuscany in 2025: Top Beautiful Towns, Villages & Must-See Destinations

As someone who calls Italy home, I can say Tuscany never fails to inspire with its enchanting mix of rolling hills, sun-kissed vineyards, and storybook villages. Whether you’re passionate about art, history, or culinary delights, Tuscany offers countless destinations that promise memorable experiences. From iconic cities like Florence and Siena to hidden villages bursting with character, you’ll find beauty and culture at every turn. Let me guide you through my favorite spots and must-see towns—each offering its own unique charm and timeless appeal—so you can make the most of your Tuscan adventure.

Key Highlights

• Tuscany offers enchanting towns, rolling hills, and hidden villages, blending art, history, and cuisine for unforgettable journeys.
• Florence dazzles with world-class art, vibrant piazzas, local food, and authentic insider experiences beyond the usual tourist paths.
• Pisa provides much more than its famous tower, boasting lively neighborhoods, historic sights, and a relaxed atmosphere perfect for deeper exploration.
• Planning day trips and choosing an ideal base enable visitors to discover Tuscany’s diverse landscapes, charming villages, and local traditions with flexibility.
• Local tips and a curated countryside trip checklist help travelers enjoy unique stays, authentic cuisine, and Tuscany’s timeless rural beauty.

Why I Love Exploring the Charming Towns of the Tuscan Countryside

Living in Italy has made me truly appreciate the magic of the Tuscan countryside. There’s a timeless charm in its rolling hills, medieval villages, and picturesque towns that draw both locals and travellers from around the world. The Tuscan region offers far more than the well-known cities; it invites you to experience its slower rhythms, immerse yourself in local traditions, and discover hidden gems that make each trip unforgettable. Whether you’re seeking scenic views, pretty hill towns, or bustling villages with unique characteristics, Tuscany’s countryside is the ideal place for enjoyment, photography, and relaxation. Every hill town and village has its own way of capturing the Italian spirit, making the area a great place to stay or use as a base for day adventures through towns Tuscany is famous for.

My Favorite Hidden Villages and Scenic Views Across Tuscany

One of the true pleasures of living in this beautiful region is the endless opportunity to explore lesser-known corners of the Tuscan countryside. I’ve found that some of the most picturesque towns and villages aren’t the ones everyone talks about, but those nestled quietly among the hills, waiting to be discovered. From tiny medieval villages atop a hill, like Pienza, to spots in the rolling landscapes of the Val d’Orcia, there’s a type of beauty in each village that’s so unique and authentic, you’ll find yourself wanting to take endless photos. Pienza, with its breathtaking views and Renaissance streets, is the kind of hill town that feels almost suspended between time and space, while San Filippo offers a small, tranquil spot for anyone seeking privacy and the healing calm of the Italian countryside.

Another favorite is the region around Chianti, where hill after hill is covered in vineyards and olive groves. I find classic Tuscan characteristics here: stone buildings, cypress-lined roads, and village squares where locals gather for a leisurely day. Driving or cycling along these winding roads, every turn reveals another scenic view—often featuring a church steeple or a medieval tower outlined against the sky. Places like Cortona shine with their artistic atmosphere and rich history, offering a great place for both relaxation and inspiration. Hidden towns Tuscany boasts—sometimes far from the main travel routes—reward those who seek them with genuine Italian hospitality and mesmerizing scenery.

When I have visitors, I always plan a day trip through the countryside, picking a village or two to explore away from the crowds. San Gimignano is perfectly perched with its famous towers and panoramic views, while Siena, though well-known, still offers winding streets and corners often missed by typical travellers. The coast and even the occasional island present a very different but equally pretty side of the region that’s perfect for those wanting to see every facet of Tuscany. What I cherish most is the way these places remain vibrant and alive without losing their historical roots. Each trip through Tuscany feels like you’re stepping into a living tapestry, and that’s why I never tire of exploring its picturesque towns, hill towns, and hidden villages—every journey is a new experience.

Unveiling the lesser-known corners of Tuscany reveals a tapestry of hidden villages and jaw-dropping vistas waiting to be discovered:

• Castiglione d’Orcia: Gaze across rolling Val d’Orcia hills, with quiet lanes leading to panoramic fortresses and charming stone squares.
• Abbey of Sant’Antimo: Hear the echo of Gregorian chants in this tranquil Romanesque abbey set among olive groves and wildflowers.
• Montemerano: Stroll beneath flower-bedecked windows and enjoy the medieval ambiance of a village untouched by time.
• Bagno Vignoni: Relax beside ancient thermal pools, where steaming waters have soothed travelers for centuries.
• Lari: Discover the flavors of artisan cherries and the hospitality of a hilltop village crowned by its imposing fortress.
• Vinci: Explore the birthplace of Leonardo da Vinci, with sweeping views of olive groves and interactive museums devoted to his genius.
• Anghiari: Meander through winding streets, each corner offering scenes straight out of a Renaissance painting, with sweeping views across the Tiber valley.

Each hidden gem offers its own unique embrace of Tuscan life, blessing visitors with a slower pace, storied beauty, and heartfelt encounters with local traditions and landscapes.

Strolling Through Historic Streets: An Insider’s Guide to Florence

If there’s one city in Italy that never fails to amaze me, it’s Florence. The character of Florence is revealed in its lively streets, the grandeur of its piazzas, and the way history seems to pulse with every step you take. Wandering through this ancient city is a totally immersive experience—from the vibrant atmosphere along the Arno River to discovering tucked-away corners that only locals know. Florence offers a dazzling array of art treasures, deep-rooted culture, and a local cuisine scene that’s as enticing as its museums. Let me share my personal favorites and tips so you can enjoy every moment as only a true insider would.

Art, Culture, and Local Cuisine Recommendations in Florence

Living in Italy, I’ve found Florence is the top city where art, culture, and local cuisine are inseparable from the Italian experience. Every travel guide agrees: Florence’s vibrant piazza life, characteristic buildings, and rich food scene make it a must for anyone wanting to enjoy authentic Italy. Start by exploring a lively piazza like Piazza della Signoria, then walk through atmospheric streets where every hotel and villa reflects centuries-old art. Art is everywhere—from the Uffizi Gallery’s Renaissance masterpieces to street art on city walls, Florence’s art scene is unrivaled in the region. It’s one reason why Florence is always a favorite choice for a day trip or an extended stay in Tuscany.

Cultural enjoyment thrives, too. You might catch a band beside the river or meet local artisans in Oltrarno—let a knowledgeable guide introduce you to traditional craftsmanship for a deeper city experience. Skip typical tours in favor of personal connections, and you’ll discover the city’s vibrant, creative heart. For food, Florence’s local cuisine shines: enjoy fresh ribollita, rich bistecca alla fiorentina, or quick bites at Mercato Centrale, all within walking distance of top sights.

Florence is an ideal base to explore the region—book hotels in the center or opt for a hotel villa just outside the city for a tranquil stay. Every choice will make your enjoyment of Florence memorable, ensuring every one of your Italian travel dreams comes true.

To truly soak up Florence’s magic, try these insider tips for art, culture, and food:

• Book tickets to major museums like the Uffizi and Accademia in advance to skip long lines.
• Wander side streets to discover local artisans crafting leather goods or hand-painted ceramics.
• Dive into foodie life with a hands-on Tuscan cooking class—homemade pasta awaits!
• Schedule an early morning walk across Ponte Vecchio for breathtaking city views minus the crowds.
• Join locals for an aperitivo at a cozy piazza bar and sample regional wines.
• Explore Oltrarno for hidden gems, quirky boutiques, and authentic trattorias far from tourist spots.
• Try inventive gelato flavors—look for shops with natural colors and seasonal ingredients.

Now, let curiosity lead you to even more unforgettable experiences around every Florentine corner.

Pisa Beyond the Tower: Unique Sights You Won’t Want to Miss

If you ask most people about Pisa, their minds instantly leap to the Leaning Tower. But, as someone who lives here in Italy, I can assure you there’s a lot more to this vibrant city than that iconic tilt! While the towers of Pisa might define its skyline, the city itself offers a rich tapestry of experiences just waiting for you to discover. Wandering around, it’s clear Pisa isn’t just a place for a quick photo stop during your travel adventures in Tuscany—it’s a town with layers of history, lively piazzas, and a local character often missed by those who only come for the day.

I always suggest starting your visit by exploring beyond the Piazza dei Miracoli. The Santa Maria della Spina church, perched dramatically along the river, is a marvel in miniature and among Pisa’s prettiest sights. For a different type of experience, the bustling Corso Italia is perfect for people-watching and soaking up the city’s student energy. The Arno riverbanks are a great place for a walk, offering views of towers, churches, and pastel buildings reflected in the water—a scene that’s quintessentially Italian, but with Pisa’s own twist. If you’re looking for a base to explore more of Tuscany, Pisa makes sense logistically too, thanks to its main train connections and its convenient location in the region.

Pisa also offers something special for lovers of local culture: the vibrant neighborhoods, the serene botanical gardens near the old city walls, and art spaces where contemporary meets tradition. Don’t miss a relaxing afternoon at one of the city’s historic bath houses, or a dip in a hotel pool if you’re craving a bit of downtime. From here, day tours and trips are easy to plan, whether you want to visit nearby towns, pretty villages, or use the city as a springboard for more adventure. Every visit gives me new reasons to enjoy Pisa more—from the pretty Santa Caterina area to hidden trattorias that deliver authentic, local flavors. Pisa isn’t just the Leaning Tower: it’s an experience, a vibrant travel destination, and, for me, one of those places in Italy you’ll want to see more, more, more over your days in Tuscany.

This table offers a quick glance at some of Pisa’s hidden gems and cultural highlights, inviting you to explore the city beyond its famous leaning tower.

Unforgettable Day Trips: Planning the Perfect Way Around Tuscany

As someone who calls Italy home, I can’t recommend enough the joy of planning a day trip or even several trips across Tuscany. Every journey here is its own adventure, and the best way to appreciate the sheer variety that this region offers is by thoughtfully crafting your Tuscany itinerary. Choosing a good base—like Florence, Siena, or even Pisa—makes it easy to explore top towns, remote villages, and unique places that capture the soul of Tuscany. When you’ve got the flexibility of a car, your travel time becomes part of the fun, letting you choose your way through winding lanes surrounded by olive groves, vineyards, and those postcard-perfect cypress trees. Driving gives you the freedom to stop whenever a beautiful view or inviting trattoria catches your eye, ensuring your trip is anything but rushed.

For travelers who prefer a more guided approach, there are plenty of tours available across the region, from small private groups to family-run excursions. I often tell friends that joining a private day tour can be the perfect way to dive deep into Tuscan history without the worry of navigating unfamiliar roads or missing must-see places. Some cruises along the Arno River or themed wine tours through Chianti add a new dimension to your trip, each offering a unique perspective that’s hard to get on your own. No matter which way you choose to explore, it’s wise to plan your journeys according to opening hours and local events—this is especially true for small towns where markets or festivals can be real highlights of the day.

When I plan my own day trips, I always leave space for spontaneity. Maybe a hidden village a local mentions at a café, or a peaceful road less traveled that just calls your name. Sometimes those last-minute choices lead to the most memorable places—the kind of spots you’d never find in a guide book. The region’s compact size means you can discover multiple treasures in one day, maximizing your choice of experiences and deepening your connection to Tuscany. With the right planning and a sense of openness, each day spent in Tuscany becomes another cherished memory in your travel story.

Pienza: Savoring Pecorino and Renaissance Beauty in Val d’Orcia

Every time I visit Pienza, I’m reminded why this small town stands as one of the jewels of the Val d’Orcia. Nestled amidst rolling hills and vast stretches of countryside, Pienza sits perfectly between Siena and Montepulciano, making it an ideal base for exploring the region. What truly sets this picturesque Renaissance village apart, though, is how it combines architectural brilliance with flavors unique to Tuscany. Walking through its harmonious streets, you immediately sense why Pienza is celebrated as the “ideal town” of the Renaissance—its balance, beauty, and design are unlike anywhere else in the region. The sweeping views over the orcia valley offer a visual feast, capturing that classic Tuscan landscape of gentle hills dotted with cypress and scattered farmhouses.

No visit to Pienza is complete without savoring its legendary pecorino cheese. The town’s creamy, aromatic pecorino is the star of every market and food shop. I love watching how locals pair slices of cheese with honey or jam, often alongside a glass of robust orcia wine. The aroma drifts through the doorways of tiny shops, filling the streets with a promise of authentic Italian taste. For me, it’s a special experience to visit a small village dairy and see the pecorino being made by hand, living proof of how culinary traditions run deep here. The cheese, with its nutty, slightly tangy profile, is as much a symbol of this countryside as the sun-baked hills themselves.

Life in Pienza moves at a slower, more soulful pace. Take time to simply enjoy the town—wander its stone lanes, step onto a panoramic terrace overlooking the orcia valley, or linger in a café with a glass of local wine. The surrounding area, including famed sites like San Quirico d’Orcia and San Giovanni d’Asso, reveals even more of the region’s beauty and character. When you stay in or near Pienza, you’re perfectly placed to enjoy both the tranquil atmosphere of the countryside and the creative spark of the Renaissance spirit. Each visit here reminds me how the best parts of Tuscany are often found in these small, beautiful villages where history, tradition, and taste blend seamlessly beneath the Tuscan sun.

Lucca’s Allure: Cycling the Walls and Discovering Its Charms

Lucca is one of those places in Tuscany that locals, like myself, find endlessly enchanting. This town’s historic walls aren’t just remnants of fortification—they’re the heart of Lucca’s daily life and charm. Unlike most Italian cities, Lucca’s walls are perfectly preserved, wide, and tree-lined, offering a 4-kilometer ring around the city center. The best way to experience their magic is simply to cycle or walk atop them, just as locals do. It’s an experience that blends the vibrancy of town life with peaceful greenery and panoramic views. Every time I cycle these walls, I’m reminded why Lucca consistently ranks as a top destination for both relaxation and discovery.

Within the walls, Lucca hides a captivating network of narrow lanes, elegant piazzas, and hidden towers. No matter the day, the city pulses with life—families on outings, visitors snapping photos, students enjoying an afternoon stroll. The towers of Lucca, especially Torre Guinigi with its rooftop oaks, invite you to climb up for striking photos and sweeping views across the old town’s red-tiled roofs. There’s something vibrant yet tranquil here, a softer rhythm that sets Lucca apart from the bustle found elsewhere in Tuscany. If you’re looking for a hotel or villa, Lucca is a great place to stay—a base for further exploration by train or guided tours throughout the region.

I always recommend embracing local flavors in charming piazzas like Piazza dell’Anfiteatro, and stopping at a café after a morning cycling the walls. The town’s vibrant energy is reflected in its local markets, inviting you to join in daily enjoyment and savor authentic Italian treats. Lucca’s villas and boutique hotels preserve that special blend of comfort and history, making every overnight stay memorable. Whether you visit by train for the day or linger longer, Lucca promises a unique Italian town experience—where past and present harmoniously coexist, and simple pleasures are everywhere. For any traveler gathering memories and beautiful photos in Tuscany, Lucca is an unmissable highlight.

Some highlights:
- Pienza (famous for its pecorino cheese)
- Montalcino (renowned for Brunello wine)
- Bagno Vignoni (unique thermal springs square)

Top Florence attractions:
- Uffizi Gallery
- Florence Cathedral (Duomo)
- Boboli Gardens

Don't miss:
- Climbing Torre Grossa
- Sampling local Vernaccia wine

Why Siena?
- Central location
- Famous Piazza del Campo
- Rich history and local cuisine

Reasons to base yourself in Lucca:
- Easy day trips to Pisa and Florence
- Historic city walls (great for biking)
- Lots of local markets and authentic food

Your Italian Journey Awaits: Pick Your Perfect Itinerary